Rory and Jess: The Later Years
by hieisdragoness18
Summary: Starts during Bon Voyage after Rory walks her grandparents to the car. What if Jess had shown up? sorry I really suck at summaries and titles so for now this is what i have. this will start during bon voyage and then skip ahead a few years to after the campaign and rory and jess' lives. rated M for later chapters. was originally called rory and jess version 2.0
1. Chapter 1

She sees him standing there, bathed in the glow of a streetlight, after walking her grandparents to their car for one last goodbye. She wonders in some far corner of her mind, how stupid she must look just standing there staring at him with her mouth slightly open. He must decide to take pity on her because suddenly he's walking towards her. That familiar smirk on his handsome face bundled up in the beat up old leather jacket that makes him look like the bad boy everyone always thought he was. Except her. She alone knew that the bad boy act was just that an act to hide behind, an excuse to not let the world in. Except her. It was always her he let in. It was always her he opened up to and only her. It was only for her that he was in this crazy town again. People would assume it was for his mother and baby sister and uncle that he came to see but the two of them knew better.

" Hey," he says when he reaches her.

" Hey," she replies with a shy smile.

" Luke called me," he explains. " He told me you were leaving and that I should come and see you off." This time her smile lights up her face. " He put all this together for you. It was all his idea."

" Really? Mom and I figured it was Sookie," He smiles and shakes his head. " I have to go thank him! Will you help me find him?" Jess smirks and jerks a thumb over his shoulder towards that diner. Rory's mouth drops open in shocked delight to see her mother and Luke locked in a passionate kiss.

" Looks like Lorelai has it covered," he intones dryly.

" Jess," she giggles and he smirks again.

" Hey, you wanna dance?" She smiles in surprise.

" I didn't know you dance," she says as she lets herself be led back to her party and the dance floor.

" There are many things you still don't know about me Miss Gilmore," he says and twirls her to her laughing delight. People clear the floor for them as the DJ that took over for Kirk puts on a slow song. The whole town watches them together but neither of them pays attention. They're too busy catching up to care.

" I got to meet Christiane Amanpour yesterday," she tells him.

" Yeah? That's great! How did that happen?" She tells him about the meeting and how embarrassed she was about meeting her idol in her pajamas. " Well at least you make an impression," he laughs.

" That's what my mom said! Anyways, she gave me her card and told me to send her some of my work and maybe she would be able to help me. I was floored! I mean this is a woman who won nine Emmy's for her journalism skills and she wants to look at _my _work!"

" Hey I've read you're work, it's nothing that you have to be ashamed of Ms. Yale News Editor," he tells her before he once more twirls her to make her laugh breathlessly. The song ends and they head over to the food tables where a blushing Luke talks softly to a grinning Lorelai.

" Hey Kid," Lorelai says when she sees to pair. " Jess."

" Aunt Lorelai," Jess replies in a fake respectful tone. Lorelai snorts and rolls her eyes. " Uncle Luke," this time the tone is real and Luke gives him a brief hug.

" Thank you Luke for the amazing party," Rory says before giving the man a sincere hug.

" It was nothing," he replies gruffly but returns the hug nonetheless.

" Right, I'm going to go see Liz and Doula before I need to go get a cavity filled," Jess says when things grow awkward. Lorelai and Rory laugh and then laugh harder when Luke says he doesn't get it. Jess turns away with a shake of his head but stops when Rory says his name softly. " I'm staying the night at the diner," he says reassuring her he isn't going to just take off. Rory smiles and says okay before leaving to go talk to Babette and Miss Patty.

Later that night after the party winds down Rory goes to Luke's diner and heads up the stairs knowing that Jess will be there waiting to see her and catch up in private. She knocks on the door to the apartment before he opens the door sans shirt and hair wet. Obviously he had just gotten out of the shower and she stands there drinking her fill of him for several moments.

" So do you want me to take a picture so you can have it on those lonely nights on the road?" She looks up and his teasing smirk is in place as he casually stands there watching her. She knows he is just trying to make her uncomfortable.

" Sure, why not?" She tosses back and quickly pulls out her cellphone and snaps a picture of him. He looks surprised for a moment before he laughs and pulls her into the apartment. He goes to the open duffle bag on his old bed and pulls out a shirt to put on.

" Want something to drink?" He asks going to the fridge.

" Sure," she says sitting on the old couch. He returns with two beers and sits next to her.

" So," He says after they both take a sip. She looks down and picks at a lose thread on the couch.

" Logan proposed," she blurts because she _has _to tell him.

" Wow," he says. " I don't remember seeing him tonight."

" I said no." She meets his gaze and continues. " It was right before graduation. He asked me in front of a bunch of people. It was awful because I couldn't answer him. He wanted me to move to California with him for his new job. He made it sound so nice but I told him I needed time. I think I was just stalling. I told him at graduation that I wasn't ready and he told me he didn't want to do the long distance thing again and that it was all or nothing. So I told him no and he left. Part of me was relieved. I'm just starting out! I'm not ready to be married to a guy like Logan. I knew my career would wind up taking a backseat to his and I just couldn't do it. It hurt though when he walked away." Jess pulled her in close for a hug and Rory realized she was crying.

" Breakups always hurt like hell," he tells her as she leans in closer inhaling his familiar scent. " Especially when you're in love with each other."

" Jess," she says and he knows where she's going, back to _that night._

" It was a long time ago Rory. You already apologized and I already forgave you. I forgave you that same night when I told you that you could tell him we slept together." Jess tilts her face up so she can look into his eyes. " _I'm _sorry Rory. For all those years ago. You didn't deserve what I did Rory you deserved so much better."

She sniffles and leans in closer to him and they sit and talk for the next hour. She tells him about Dean and their second failed go round, the Life and Death Brigade, living with Pairs and her time off of Yale and why she left and then why she went back. Because of _him _and what he said to her. He tells her why he left all those years ago and finding his father out in California and how he made his way back across the country. About the time he was living in New York and came back for his mother's wedding. He tells her how he met his partners at the publishing house and how he wrote The Subsect and how she was his inspiration for his writing. They talk about the classes she took while at Yale and that sometimes she would use the things he said when she was debating literature in class and how she still finds Hemingway boring as all get out but can tolerate him more now. He smiles and tells her I told you so before noticing the time.

" As fun as this is, Rory you need to get up early tomorrow and take your first real steps to fulfilling your dream."

" My first steps to fulfilling my dream huh? Now who's the cheerleader?" she teases.

" Shush you," he says and playfully shoves her. He stands up and grabs his jacket and she puts her shoes back on, not remembering when she had slipped them off, before following him downstairs. They see Luke down there putting away the last of the party leftovers. Rory gives him another hug and says goodnight before she leaves with Jess. The walk to her house is made in silence but it's a pleasant one. She slips her hand into his after the first block and he doesn't bother to hide his grin from her. All too soon they reach her house. The lights are on and she can just see her mother inside. She turns to him with sadness in her eyes.

" Jess I-" he steps forward and gives her a soft kiss on the lips.

" Don't worry. We'll say goodbye in the morning," he says hugging her to him. She breathes him in deeply and gives a shaky okay. He kisses her forehead before turning and walking back to the diner. " Go inside Gilmore before it starts raining again," he calls over his shoulder. She smiles and does what he says.

It's just after five in the morning when she and her mother sip coffee in Luke's the next day. She savors this, her last breakfast at Luke's until who knows when. She smiles at her mother and Luke and their gentle flirting. She knows that this time they will work out and she can't wait until their wedding. Jess comes stumbling downstairs freshly showered but still half asleep just as Luke comes out of the kitchen with breakfast for all of them.

" Well aren't you graceful this morning," Lorelai quips. Jess mumbles something unintelligible and steals some of Rory's coffee.

" Hey! Mine!" She laughs and takes the cup back. " Who knows when I'll be able to drink Luke's heavenly blend again!" Jess blinks blurrily at her and she laughs at him before passing him the rest of the cup and getting up to help herself to a new cup from behind the counter. The small group eat finish their food and then it's time for Rory and Lorelai to leave for the airport.

" Why don't you come both with us?" Lorelai offers when everyone looks on the verge of misery. Jess's head snaps up at the offer and Lorelai meets his gaze with a pained smile. They all pile into Lorelai's jeep with Rory and Jess in the back holding hands and leaning into each other. Rory and Lorelai talk the whole way while Luke and Jess are content to just sit and listen. All too soon they arrive at the airport.

" So this is it Kid," Lorelai says when the other three aren't allowed to go on without a ticket.

" Yeah," Rory says trying hard not to cry and failing. The goodbyes are tearful except Jess. He manages to hold his back but his eyes are watery when he hugs Rory. He takes off his leather jacket and slips it around her shoulders. Finally Rory walks away, she gets to the edge of the security checkpoint before she turns around for one last look. Her mom and Luke and standing with arms around each other and Jess stands next to them hands shoved into his jeans pockets. Rory makes a strangled noise, drops her bags and runs back to her mom for one last round of hugs. She breaks away finally and hugs Luke again before turning to Jess. He holds her for a moment before he backs away enough to kiss her goodbye.

" Go get 'em Lorelai Leigh Gilmore," he says and plants a kiss on her forehead before giving her a gentle push towards the plane. She gives him a watery smile and hugs her mom again before leaving. This time she makes it past the checkpoint and waves before walking away. They watch until she is out of sight and then they watch her plane take off twenty minutes later before Luke drives them back to Stars Hallow. Lorelai sits in the passenger seat and stares out the window tears falling until Jess leans forward and puts his hand on her shoulder. " She'll be alright," he tells her though his own voice is horse from trying not to let tears fall. Lorelai nods and dries her eyes just as they enter the town.

On the plane Rory finds her seat and takes Jess' book from her bag before she settles in for the short flight, his jacket collar turned up so she can just tilt her head and smell his scent still. Jess was right she was taking her first steps to fulfilling her dream and she was determined to make everyone who loved her proud of the work she will do.


	2. Chapter 2

A/N: Sorry this took me so long to get out everyone! The plot bunnies were fighting as to which way this should go so i sent them to the corner to hash it out. Also as a warning this chapter contains Tory. Tristan would not let me leave him out of this story and was entirely too insistent on what would happen. don't worry this _will not_ be a story that has rory and tristan together other than in this chapter. they will be friends through and he will show up now and again. And now on with the story.

* * *

Rory sat in a quiet little café in North Carolina sipping coffee and finishing up her latest article for the campaign. She was quite relieved that she only had two more stops before the campaign ended. Being on the road for over a year was exhausting. She was looking forward to returning home to Stars Hollow for some relaxation, not to mention the fact that she would be in one place for longer than three days. Getting home in time for the holidays was going to be wonderful and soon she would be walking own the aisle in her mother's wedding to Luke. The bell over the door to the café startled her out of her daydreaming and back into proofing her article. Suddenly a voice disturbed her once more.

" Well hello Mary," Rory's head snapped up from her laptop and her gaze met one she never thought she's see again. " Fancy meeting you here."

" Tristan!" He smirked at her as she jumped up to give him a hug. " Oh my God! What are you doing here?" Tristan laughed at her.

" I live around here," he replied. Rory gaped at him.

" You do?" Tristan laughed and nodded. " Wow! I never thought we'd see each other again! How are you?"

" Me neither. Can I sit?" he asked putting one hand on the back of the chair next to her. She flushed.

" Oh of course! Please sit. Sit," Tristan sat and Rory leaned forward. " So come on tell me what you've been up to all these years. The last time we saw each other you were going to military school. How'd that turn out?"

" You never change," Tristan laughed. " Well Ms. Reporter military school was fine. It was quite the change though after Chilton and it took me several months to adjust but I wound up liking it. I did a four-year stint in the Army and just got back from a Special Forces tour in Iraq. I got back to the States two days ago and I've been staying with a buddy of mine who live a few blocks away. I've been trying to figure out what I want to do now that I'm no longer in the military."

" Wow Tristan that's amazing!"

" Yeah. Hey do you wanna get out of here? Maybe go to dinner?"

" I'd love to," Rory smiled. " I do have to finish this article and get it to my boss in the next half hour though."

" Okay well how about we meet in an hour and I'll take you out? Where are you staying?"

" That sounds good to me. I'm staying at the Holiday Inn just across the street," she said point to the hotel that was visible out the café window.

" I'm in room 815."

" Great. I'll see you in an hour," he leaned in close to her and gave her a quick kiss on the cheek. " Bye Mary."

Rory laughed and shook her head as she watched him walk out. She quickly finished up the last bit of her article before emailing it to her boss. Minutes later she was packing up her laptop and digging her phone out of her purse. She hit the speed dial for her mom and was disappointed to get the answering machine at the house. She left a quick message about going to dinner with a friend and promised to call the next day while she crossed the lobby. She was putting on the finishing touches to her makeup, after a quick shower where she shaved her legs, when she realized that she was acting like this was a date.

Was that what this was? Or was this just dinner with an old friend? One who used to have a serious crush on her. _No, it's just dinner_. _Stop trying to see things that aren't there. _She scolded herself. After all Tristan would have said if it was a date. Rory was making the final adjustments of her sweater dress when there was a knock on her door. Crossing the small room she opened the door to Tristan in the hallway. He looked quite nice in dark jeans and a dark green turtleneck.

" Hey," she smiled.

" Wow Mar, you look beautiful," Rory blushed and muttered a thank you. She joined him in the hall and was about to close her door when he spoke again. " Um Rory I think you're forgetting something."

" Huh?"

" Shoes," he said looking down. Sure enough she was standing there in the hall only in her stockings.

" Rats," she muttered and he laughed putting her at ease. " Why don't you come in for a second," she said opening the door again. She hurriedly dug through her bag in the little nook by the bathroom door while Tristan sat on the bed and patiently waited for her. " Okay I'm ready," she said once she had stepped into her heels and had grabbed her purse, which had her room key and cellphone along with her wallet.

Tristan smiled and escorted her out of the hotel room and to the elevator. Once outside the hotel they talked about where they wanted to go. Since neither of them knew the area very well they wound up going back inside and asking the desk clerk who recommended an Italian restaurant, which wasn't too far away. They took a cab and soon they were seated at a cozy table in the fairly crowed restaurant.

" This place smells amazing," Rory commented inhaling.

" Yeah it does. I'm starving," Tristan said cracking open the menu. Soon the waitress appeared. " I'm going to get the spaghetti," he told the waitress.

" And for you miss?" The older woman asked Rory.

" I'll have the lasagna please"

" Okay. Would either of you care for something to drink?" Tristan looked at Rory.

" Want to share a bottle of wine?"

" Sure, why not?" Tristan smiled and asked for a bottle of red wine. The waitress left and returned a few minutes later with their wine and a basket of garlic bread. Rory took a bite of bread and hummed in appreciation. " This is so good!"

" I'm glad," Tristan said as he sipped some of his wine. Rory shyly looked over at him.

" Can I ask you something Tristan?"

" Of course," he took a bite of bread himself.

" Um, I feel silly even asking this, is this a date?" Rory asked and then took a large gulp of her wine. Tristan raised his eyebrows.

" Do you want it to be?" he asked. Rory looked down at the table.

" I'm not sure," she answered truthfully. " I'm not seeing anyone at the moment so that's not the problem."

" I'm not seeing anyone either, in case you were wondering."

" Yeah I was."

"Then what is the problem with the idea of this being a date?" Tristan questioned. Rory opened her mouth to answer but stopped when the waitress appeared with their food. They thanked her and dug into the food.

" There isn't a problem per say," Rory started after a few moments. " It's not that I wouldn't enjoy being on a date with you. This isn't high school anymore." Tristan snorted a laugh. " Things are just a little, well complicated."

" How?" Tristan asked. He didn't seem upset just curious.

" There is this guy," Rory started.

" Ahh," Tristan smiled. " And you like him."

" Well yes, but it's more than that. We dated. Back in senior year of high school. I dated him after Dean broke up with me at the Dance Marathon in front of everyone."

" Wait, Dean broke up with you in public? In front of a bunch of people?" Tristan demanded sharply. Rory winced.

" Yeah. It was bad. But honestly it was partly my fault. I was too focused on Jess," Tristan interrupted.

" Jess?"

" My second boyfriend. He's Luke's nephew."

" Okay I think you need to start at the beginning cause I'm getting lost here." Rory laughed nervously and launched into the tail as they both finished up their dinner. " Wow," Tristan said twenty minutes later after hearing all about Rory's love life for the past seven years.

" Yeah," Rory said with a blush.

" So complicated. Got it," Rory blushed harder and stared at the table.

" You want dessert?" Tristan asked. Rory looked up and saw he was smiling gently at her. She smiled and nodded. Dessert was eaten in silence and Tristan picked up the check. " Since this is going to be our only date and all I'm paying," he said when she offered to pay for her half. " What do you say we walk back the hotel and you try and defend dating _Logan Huntsburger_ to me."

" You know Logan?" She asked as he helped her into her coat.

" I knew him. We went to the same middle school for about a month before he got kicked out." Tristan said with a grimace. " I thought you would have had better taste than to date _him_." Rory smacked his arm lightly as they walked.

" He wasn't that bad," she laughed. Tristan pulled a face at her and she laughed. " Well okay he had his bad points. If it makes you feel any better Jess hated him too."

" They met?" Tristan asked as he held open the lobby door for her.

" Yep," Rory said as they walked into the elevator. " And it was definitely some meeting." Rory told him all about it as the lift took them to her floor and as they walked into her room. Rory kicked off her heels when they got inside and Tristan helped himself to an unopened water bottle she had left on the little beside table and then sat on her bed. They spent the next couple hours catching up on each other's lives.

" Well Mary, I've got to say you certainly have changed," Tristan called as Rory was in the bathroom changing. " Or maybe I start calling you Maggie." Tristan was lounging on the bed when she came back out.

" Maggie?" Rory questioned as she pushed his feet off the end of her bed.

" Yeah you know Mary Magdalene," Tristan laughed as he took his shoes off before putting his feet back up. Rory bite her lip as she sat down on the bed.

" So you think I've become a Maggie?" She questioned gazing down at the bedspread. Tristan chuckled and scooted closer to her so he could give her a hug.

" Nah. I think you just made a couple bad calls is all," he said into her hair. Rory smiled and drew back to look at him. She sucked in a sharp breath when she realized just how close they were. Tristan's eyes darkened and he slowly moved in to kiss her.

" Tristan?" She questioned when the kiss turned hungry and his hands started exploring.

" Shh. One night Rory. That's all it has to be. I just want you so badly. Please," Rory pulled away and searched his face for several long minutes before she leaned back in to kiss him.

" I'll have to leave by 9am," she warned him.

" Okay," he breathed as he shifted them on the bed. " That's hours away," he smiled. After that they didn't say anything for a long time.

The next morning Rory said goodbye to Tristan after breakfast and a shared shower before she checked out of the hotel and met up with the rest of the campaign reporters at the bus station.

The days flew by and soon it was Super Tuesday and then she was writing her last article before she went back home. Then it was the next day and she was calling her mom to tell her that her flight was leaving in two hours and she couldn't wait to get home. After an extra hour in the air due to bad weather Rory finally landed in Hartford. She was headed to get a taxi when she heard her name being called.

" Jess!" Rory exclaimed as she ran to him.

" Hey stranger," he said as he caught her in a hug.

" What are you doing here?" She asked him.

" Nothing much, I like to hang out here and pick up women," Jess quipped.

" Jess," she said his name mixed with exasperation and affection.

" Lorelai had an emergency at the Dragonfly and I happened to be in town," he explained as he walked them towards the exit and his car.

" Is everything okay?"

" Seemed to be. There is a wedding or some sort of party there in the next few days and someone wasn't happy about something or other. I wasn't paying much attention to her explanation," Jess told her as he put her luggage in the trunk. He got into the car and turned to her. " So you want to tell me why you looked panicked when you saw me or should I just guess?" Rory bite her bottom lip and stared out the window for a long time. " Rory?"

" I ran into Tristan last week in North Carolina," She started.

" Tristan?" Jess questioned trying to remember when she had mentioned that name before. " He was that guy you knew in high school right? Tried to get you away from Dean?"

" Yeah," she sighed. There was no good way to tell him this. " I ran into him at a café where I was working on my article. We went to dinner and talked," Jess sat expressionless. " Mostly we talked about my love life these last few years. I told him everything. He walked me back to the hotel afterwards and we spent the next few hours just catching up," Rory paused and Jess spoke.

" Just tell me Rory."

" We slept together," Jess flinched. " It didn't mean anything Jess. I swear that to you. It was just a one-night stand. When I left in the morning we agreed to keep in touch occasionally and that was all. Please don't be mad," she whispered. Jess took a deep breath and ran a hand over his face.

" I'm not mad Rory," he told her softly.

" You aren't?" She asked hopeful. He sighed and dragged his hand through his hair.

" No. I'm not. You and I, we aren't dating. We haven't been dating. You are allowed to sleep with whoever you want Rory. I understand that you wanted to tell me because you felt you owed it to me but it's okay you, you don't owe me an explanation every time you sleep with someone else."

" I don't want to sleep with anyone else," Rory said when Jess was about to start the car. He stopped and looked at her. " I want to be with you Jess. I miss you. I want us to try again. I've wanted it for so long Jess. I couldn't tell you that when you came to see me last year. I wanted you so badly but I was afraid that I was just rebounding from Logan and I didn't want you to only be my rebound. After the thing with Tristan I knew for certain that you weren't going to be my rebound. I love you-,"

Jess practically dove across the seat as he kissed her. This was what they had been missing for so long. Rory returned the kiss with as much passion as he put into it, their tongues intertwining and both of them breathing heavily. The sound of a plane taking off broke them out of their haze. Jess smiled softly at Rory's dazed look before he shifted back into the driver's seat and started the car.

" I love you too," he told her taking her hand as they pulled out of the lot. Rory smiled and settled in for the ride to Stars Hallow.

* * *

A/N 2: this story won't be much longer. probably only a chapter or two. reviews are love.


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